Table 1.
Systematic characterization of synthesized triazolopeptides 1–23.
| No. | Sequence | RT [min.] | General Formula | Calc. MS [m/z] | Meas. MS [m/z] |
|---|---|---|---|---|---|
| “linker” subseries | |||||
| 1 | Lys(Har)-GlyΨ[Trl]Arg | 11.98 1 | C22H43N13O4 | 554.3634 4 | 554.3640 4 |
| 2 | D-Lys(Har)-GlyΨ[Trl]Arg | 11.96 1 | C22H43N13O4 | 554.3634 4 | 554.3656 4 |
| 3 | Lys(Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 13.22 1 | C25H46N16O4 | 635.3961 4 | 635.3979 4 |
| 4 | D-Lys(Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 13.30 1 | C25H46N16O4 | 635.3961 4 | 635.3980 4 |
| 5 | D-Lys(D-Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 13.33 1 | C25H46N16O4 | 635.3961 4 | 635.3982 4 |
| 6 | Lys(Har)-Pro-GlyΨ[Trl]Arg | 14.65 1 | C27H50N14O5 | 651.4161 4 | 651.4187 4 |
| 7 | D-Lys(Har)-Pro-GlyΨ[Trl]Arg | 14.65 1 | C27H50N14O5 | 651.4161 4 | 651.4190 4 |
| 8 | Lys(Har)-Phe-GlyΨ[Trl]Arg | 14.89 2 | C31H52N14O5 | 701.4318 4 | 701.4339 4 |
| 9 | D-Lys(Har)-Phe-GlyΨ[Trl]Arg | 15.04 2 | C31H52N14O5 | 701.4318 4 | 701.4338 4 |
| 10 | Lys(Har)-GlyΨ[Trl]Ala-Arg | 13.17 1 | C25H48N14O5 | 625.4005 4 | 625.3994 4 |
| 11 | Lys(Har)-GlyΨ[Trl]Gly-Arg | 12.19 1 | C24H46N14O5 | 611.3848 4 | 611.3878 4 |
| 12 | Har-Pro-GlyΨ[Trl]Arg | 13.78 1 | C21H38N12O4 | 523.3212 4 | 523.3221 4 |
| 13 | Har-GlyΨ[Trl]GlyΨ[Trl]GlyΨ[Trl]Arg | 14.52 1 | C22H37N17O3 | 588.3338 4 | 588.3362 4 |
| “arm” subseries | |||||
| 14 | Lys(Fmoc-Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 16.50 3 | C40H56N16O6 | 429.2357 5 | 429.2371 5 |
| 15 | D-Lys(Fmoc-Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 16.53 3 | C40H56N16O6 | 429.2357 5 | 429.2373 5 |
| 16 | Har-Lys-GlyΨ[Trl]GlyΨ[Trl]Arg | 13.05 1 | C25H46N16O4 | 635.3961 4 | 635.3991 4 |
| 17 | Dab(Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 12.46 1 | C23H42N16O4 | 607.3648 4 | 607.3675 4 |
| 18 | Dap(Har)-GlyΨ[Trl]GlyΨ[Trl]Arg | 11.92 1 | C22H40N16O4 | 593.3491 4 | 593.3517 4 |
| 19 | Har-6Ahx-GlyΨ[Trl]GlyΨ[Trl]]Arg | 16.83 1 | C25H45N15O4 | 620.3852 4 | 620.3878 4 |
| 20 | Har-5Ava-GlyΨ[Trl]GlyΨ[Trl]Arg | 15.23 1 | C24H43N15O4 | 606.3695 4 | 606.3721 4 |
| 21 | Har-Ala-GlyΨ[Trl]GlyΨ[Trl]]Arg | 13.46 1 | C22H39N15O4 | 578.3382 4 | 578.3406 4 |
| 22 | Har-Gly-GlyΨ[Trl]GlyΨ[Trl]Arg | 13.06 1 | C21H37N15O4 | 564.3226 4 | 564.3244 4 |
| 23 | Har-GlyΨ[Trl]GlyΨ[Trl]Arg | 13.06 1 | C19H34N14O3 | 507.3020 4 | 507.3011 4 |
1 linear increase of phase B from 1% to 21% in 20 min; 2 linear increase of phase B from 10% to 40% in 20 min; 3 linear increase of phase B from 20% to 40% in 20 min; 4 pseudomolecular ion [M + H]+; 5 pseudomolecular ion [M + 2H]2+.